Bad Bunny Redefines Latin Masculinity Through Fashion

Bad Bunny has always lived in dualities, existing in the space between softness and strength, fame and humility, rebellion and tenderness. He wears skirts and pearls with the same ease he once wore basketball shorts and gold chains, proving that masculinity can be both grounded and expressive, both delicate and bold. Through his music, he sings of heartbreak and power, love and loss, fame and home, reminding us that emotion and masculinity are not opposites but companions.

Beneath the global icon remains the kid from Vega Baja, Puerto Rico, creating music that speaks to the truth of who he is and where he comes from. From the underground pulse of Soy Peor to the elegance of the Met Gala, Benito Antonio Martínez Ocasio has transformed fashion, fame, and feeling into a manifesto that challenges the limits of what Latin masculinity has been allowed to be. His artistry refuses the outdated idea that being a man requires silence or hardness, and instead offers a new vision of strength – one that is vulnerable, fearless, and unapologetically free.

The Calle Aesthetic

When Bad Bunny first appeared in 2016 with Soy Peor, he looked like every guy from the block: oversized hoodies, shaved lines in his hair, and tinted sunglasses that never came off. It was the aesthetic of Puerto Rican street culture: raw, confident, and expressive. His early fashion choices mirrored the sounds of his trap anthems, blending the swagger of reggaetón with the grit of hip-hop.

In 2019, the music video for “Caro” was released, opening with a shot of his nails being painted before the camera cuts to a version of himself portrayed by a woman. The video explores gender fluidity, self-worth, and beauty standards, showing Bad Bunny surrounded by models of all gender expressions and body types. At the time, it was a bold statement in a genre often defined by hypermasculinity, signaling his intent to redefine what it means to be a man in reggaetón and in Latin pop culture at large.

But even then, there were hints that he wasn’t here to play by the rules. In videos like “Chambea” and “Estamos Bien“, he fused bold color palettes with self-styled outfits that leaned more toward the avant-garde than the macho. He didn’t fit neatly into the archetype of the Latin male artist from the get-go, instead opting for a more playful, eccentric, and unpredictable approach.

Bad Bunny’s fashion sense became an extension of his rebellion. While mainstream reggaetón was still dominated by hypermasculine posturing, he wore crop tops, painted his nails, and experimented with silhouettes traditionally coded as feminine. What made it radical was that he never treated it like a costume. It was just him, comfortable in both the softness and strength of his identity.

Skirts, Pearls, and Protest

In February 2020, Bad Bunny appeared on The Tonight Show Starring Jimmy Fallon wearing a white skirt and a shirt that read, “Mataron a Alexa, no a un hombre con falda” (“They killed Alexa, not a man in a skirt”). The message referred to the murder of Alexa Negrón Luciano, a trans woman in Puerto Rico, and it marked a turning point for how the world saw him. It wasn’t about shock value. It was about using visibility to confront violence and machismo directly.

That same year, he released “Yo Perreo Sola”, performing in drag and closing the video with a message that read, “Si no quiere bailar contigo, respeta. Ella perrea sola.” (“If she doesn’t want to dance with you, respect her. She twerks alone.”) The video exploded online not just for its visuals, but also for demanding respect for women in a genre that has often objectified them.

Those choices — skirts, heels, wigs, glitter — became symbols of defiance, rejecting the idea that softness and masculinity cannot coexist. For millions of fans across Latin America, he was proof that you could embrace vulnerability and still carry power.

Couture Meets Calle

By the time he appeared at the 2022 Met Gala wearing a custom Burberry gown with puffed sleeves, Bad Bunny had fully crossed into fashion icon territory. Yet even surrounded by haute couture, he brought the same authenticity that defined his early days. The look, inspired by 18th-century silhouettes, referenced Caribbean colonial history bringing together masculine and feminine styles. He did it again at the 2025 Met Gala, where he donned a pava, a traditional hat made of palm leaves typically worn by jíbaros, or Puerto Rican farmers from the countryside, in collaboration with Boricua designer Neysha De León and the creative team at Prada, who designed the rest of his outfit.

As we know, Bad Bunny is no stranger to leaning into the unusual. He’s collaborated with some of the biggest names in the game, including Jacquemus, where he modeled floral prints, silk shirts, and playful pastels. What stood out most was that none of it felt like performance. He wasn’t borrowing femininity for shock; he was simply expanding what masculinity could look like by fusing streetwear’s edge with couture’s experimentation while proving that authenticity can live in both a basketball jersey and a tailored skirt.

The New Language of Masculinity

For decades, Latin masculinity has been defined by machismo: stoicism, dominance, and control. Bad Bunny has rewritten that script by making expression itself the new form of strength. He cries on stage, sings about heartbreak, paints his nails, and wears pearl necklaces while spitting bars about loyalty and love.

This softer version of masculinity is not weakness. It is liberation. He shows that identity is not a box but a spectrum, one that allows men to feel deeply without fear of ridicule. That message resonates deeply in cultures where vulnerability is often dismissed as feminine or fragile.

His style, much like his music, creates a safe space for emotion, experimentation, and honesty. Every look becomes a statement: that Caribbean men can be both fierce and tender, fashionable and grounded, global and still del barrio.

From Vega Baja to Versace

Bad Bunny’s journey from the streets of Vega Baja to the front row of fashion week isn’t about reinvention, but rather about evolution. He didn’t abandon his roots to enter the world of couture. He carried them with him, transforming them into art.

When he walks a runway or posts a fit pic in a skirt, he carries generations of Caribbean men who have been taught to hide their softness. When he collaborates with luxury brands, he invites them to learn his language instead of erasing it. In doing so, he expands the meaning of masculinity, identity, and Latinidad itself.

Bad Bunny’s fashion story is not just about clothes. It is about courage, the kind that lets you wear color, love openly, and redefine what it means to be seen.

Ashley Rivera Mercado was born in Yauco, Puerto Rico and raised in Orlando, Florida. She is the jefa at the non-profit Mujeres in Marketing.